311 is the gematriya of "ish", man. It is also the gematriya of "ha'isha", the woman; whereas "isha" is gematriya 306. "I find "ha'isha" more bitter than death" (Koheles 7:26); when the wife takes on the husband's role in marriage (so her gematriya equals his) its more bitter to him than death (Maharsha in Yevamos 63, I think).